Recoverable Pd/C catalyst mediated dehydrogenation of sterols and an improved synthesis of 1α-hydroxydehydroepiandrosterone

Steroids. 2012 Nov;77(13):1419-22. doi: 10.1016/j.steroids.2012.08.018. Epub 2012 Sep 18.

Abstract

A novel recyclable Pd/C catalyst mediated dehydrogenation of sterols is developed. The conversion of sterols to 1,4,6-trien-3-ones is best achieved with Pd/C as a catalyst (10%) in the presence of six equivalents of allyl diethyl phosphate (ADP) and excess amount of sodium carbonate in DMF under vigorous reflux conditions. This transformation gives 17,17-ethylenedioxyandrost-1,4,6-trien-3-one in better yield than that of DDQ oxidation and thus provides an improved synthesis of 1α-hydroxydehydroepiandrosterone from DHEA.

Publication types

  • Letter
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbon / chemistry*
  • Catalysis
  • Chemistry Techniques, Synthetic
  • Dehydroepiandrosterone / analogs & derivatives*
  • Dehydroepiandrosterone / chemical synthesis
  • Dehydroepiandrosterone / chemistry
  • Hydrogenation
  • Palladium / chemistry*
  • Sterols / chemistry*

Substances

  • Sterols
  • 1-hydroxydehydroepiandrosterone
  • Dehydroepiandrosterone
  • Palladium
  • Carbon